RS50843B - Viral polymerase inhibitors - Google Patents

Viral polymerase inhibitors

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Publication number
RS50843B
RS50843B YUP-70/04A YUP7004A RS50843B RS 50843 B RS50843 B RS 50843B YU P7004 A YUP7004 A YU P7004A RS 50843 B RS50843 B RS 50843B
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RS
Serbia
Prior art keywords
alkyl
cycloalkyl
het
aryl
independently
Prior art date
Application number
YUP-70/04A
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Serbian (sr)
Inventor
Sylvie Goulet
Eric Jolicoeur
George Kukolj
James Gillard
Pierre Louis Beaulieu
Gulrez Fazal
Martin Poirier
Marc-André Poupart
Youla S. Tsantrizos
Jean Rancourt
Original Assignee
Boehringer Ingelheim (Canada) Ltd.
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Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26975871&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=RS50843(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Boehringer Ingelheim (Canada) Ltd. filed Critical Boehringer Ingelheim (Canada) Ltd.
Publication of RS7004A publication Critical patent/RS7004A/en
Publication of RS50843B publication Critical patent/RS50843B/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/20—Antivirals for DNA viruses
    • A61P31/22—Antivirals for DNA viruses for herpes viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
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  • General Chemical & Material Sciences (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
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  • Virology (AREA)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Indole Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Saccharide Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

Enantiomer, dijastereoizomer ili tautomer jedinjenja predstavljenog formulom II:pri čemu:R1 izabran iz grupe koja se sastoji od: H, (C1-6alkila eventualno supstituisanog sa:- halogenom, OR11, SR11 ili N(R12)2, pri čemu R11 i svaki R12 jeste nezavisno H, (C1-6)a1kil, (C3-7)cikloalkil, (C1-6)alkil- (C3-7)cikloalkil, (C1-6)alkil-aril ili (C1-6) alkil-Het, a pomenuti aril ili Het su eventualno supstituisani sa R10; ili su oba R12 međusobno kovalentno vezana i sa azotom za koji su vezani obrazuju 5, 6 ili 7 - člani zasićeni heterocikl;R2 je izabran između: halogena, R21, OR21, SR21, COOR21, SO2N(R22)2 N(R22)2, CON(R22)2, NR22C(O)R22 ili NR22C(O)NR22, pri čemu R21 i svaki R22 jeste nezavisno H, (C1-6 alkil, haloalkil, (C2-6)alkenil, (C3-7)cikloalkil, (C2-6)alkinil, (C5-7)cikloalkenil, 6 ili 10 - člani aril ili Het, a pomenuti R21 i R22 su eventualno supstituisani sa R20;ili su oba R22 međusobno vezana tako da obrazuju 5, 6 ili 7 - člani zasićeni heterocikl sa azotom za koji su vezani;R3 izabran između (C1-6) alkila, haloalkila, (C3-7)cikloalkila, (C5-7)cikloalkenila, (C6-10) bicikloalkila, (C6-10)bicikloalkenila, 6 - ili 10 - članog arila, Het, (C1-6)alkil - arila ili (C1-6)alkil -Het,a pomenuti alkil, cikloalkil, cikloalkenil, bicikloalkil, bicikloalkenil, aril, Het, alkil - aril i alkil - Het su eventualno supstituisani sa od 1 do 4 supstituenta izabrana između: halogena, ilia) (C1-6) alkila eventualno supstituisanog sa:- OR31 ili SR31, pri čemu R31 jeste H, (C1-6alkil), (C3-7)cikloalkil, (C1-6)alkil - (C3-7) cikloalkil, aril, Het (C1-6 alkil - aril ili (C1-6) alkil - Het; ili- N(R32)2, pri čemu svaki R32 jeste nezavisno H, (C1-6) alkil, (C3-7) cikloalkil, (C1-6) alkil - (C3-7) cikloalkil, aril, Het, (C1-6) alkil - aril ili (C1-6) alkil - Het; ili su oba R32 međusobno kovalentno vezana i sa azotom za koji su vezani obrazuju 5, 6 ili 7 -člani zasićeni heterocikl;b) OR33, pri čemu R33 jeste H, (C1-6)alkil, (C3-7)cikloalkil ili (C1-6) alkil - (C3-7) cikloalkil, aril, Het, (C1-6) alkil - aril ili (C1-6) alkil - Het;c) SR34, pri čemu R34 jeste H, (C1-6)alkil, (C3-7)cikloalkil, ili (C1-6)alkil - (C3-7) cikloalkil, aril, Het, (C1-6) alkil – aril ili (C1-6) alkil - Het; id) N(R35)2, pri čemu svaki R35 jeste nezavisno H, (C1-6) alkil, (C3-7) cikloalkil, (C1-6) alkil - (C3-7)cikloalkil, aril, Het, (C1-6)alkil - aril ili (C1-6)alkil - Het; ili su oba R35 međusobno kovalentno vezana i sa azotom za koji su vezani obrazuju 5, 6 ili 7 - člani zasićeni heterocikl;K jeste N ili CR4, pri čemu R4 jeste H, halogen, (C1-6) alkil, haloalkil, (C3-7) cikloalkil ili (C1-6) alkil - (C3-7) cikloalkil; ili R4 jeste OR41 ili SR41, COR41 ili NR41COR41, pri čemu svaki R41 jeste nezavisno H, (C1-6)alkil, (C3-7)cikloalkil ili (C1-6alkil- (C3-7)cikloalkil; ili R4 jeste NR42R43, pri čemAn enantiomer, diastereoisomer or tautomer of a compound represented by formula II: wherein: R 1 is selected from the group consisting of: H, (C 1-6 alkyl optionally substituted by: - halogen, OR 11, SR 11 or N (R 12) 2, wherein R 11 and each R12 is independently H, (C1-6) alkyl, (C3-7) cycloalkyl, (C1-6) alkyl- (C3-7) cycloalkyl, (C1-6) alkyl-aryl or (C1-6) alkyl-Het , and said aryl or Het is optionally substituted with R10; or both R12 are covalently bonded to each other and to the nitrogen to which they are attached form a 5, 6 or 7-membered saturated heterocycle; R2 is selected from: halogen, R21, OR21, SR21. COOR21, SO2N (R22) 2 N (R22) 2, CON (R22) 2, NR22C (O) R22 or NR22C (O) NR22, wherein R21 and each R22 are independently H, (C1-6 alkyl, haloalkyl, ( C2-6) alkenyl, (C3-7) cycloalkyl, (C2-6) alkynyl, (C5-7) cycloalkenyl, 6 or 10 membered aryl or Het, said R21 and R22 being optionally substituted by R20; R22 interconnected to form 5, 6 or 7-membered saturated heterocycle with nitrogen to which they are attached R3 is selected from (C1-6) alkyl, haloalkyl, (C3-7) cycloalkyl, (C5-7) cycloalkenyl, (C6-10) bicycloalkyl, (C6-10) bicycloalkenyl, 6- or 10-membered aryl. Het, (C1-6) alkyl-aryl or (C1-6) alkyl-Het, and said alkyl, cycloalkyl, cycloalkenyl, bicycloalkyl, bicycloalkenyl, aryl, Het, alkyl-aryl and alkyl-Het are optionally substituted with from 1 to 4 substituents selected from: halogen, or aa) (C1-6) alkyl optionally substituted by: - OR31 or SR31, wherein R31 is H, (C1-6alkyl), (C3-7) cycloalkyl, (C1-6) alkyl - (C3-7) cycloalkyl, aryl, Het (C1-6 alkyl-aryl or (C1-6) alkyl-Het; or - N (R32) 2, wherein each R32 is independently H, (C1-6) alkyl, (C3-7) cycloalkyl, (C1-6) alkyl - (C3-7) cycloalkyl, aryl, Het, (C1-6) -6) alkyl-aryl or (C1-6) alkyl-Het; or both R32 are covalently bonded to each other and to the nitrogen to which they are attached form a 5, 6 or 7-membered saturated heterocycle; b) OR33, wherein R33 is H, (C1-6) alkyl, (C3-7) cycloalkyl or ( C1-6) alkyl - (C3-7) cycloalkyl, aryl, Het, (C1-6) alkyl-aryl or (C1-6) alkyl-Het; c) SR34, wherein R34 is H, (C1-6) alkyl, (C3-7) cycloalkyl, or (C1-6) alkyl - (C3-7) cycloalkyl, aryl, Het, (C1-6) alkyl-aryl or (C1-6) alkyl-Het; id) N (R35) 2, wherein each R35 is independently H, (C1-6) alkyl, (C3-7) cycloalkyl, (C1-6) alkyl - (C3-7) cycloalkyl, aryl, Het, (C1 -6) alkyl-aryl or (C1-6) alkyl-Het; or both R35 is covalently bonded to each other and to the nitrogen to which they are attached form a 5, 6 or 7-membered saturated heterocycle; K is N or CR4, where R4 is H, halogen, (C1-6) alkyl, haloalkyl, (C3 -7) cycloalkyl or (C1-6) alkyl - (C3-7) cycloalkyl; or R4 is OR41 or SR41, COR41 or NR41COR41, wherein each R41 is independently H, (C1-6) alkyl, (C3-7) cycloalkyl or (C1-6alkyl- (C3-7) cycloalkyl; or R4 is NR42R43. at what

YUP-70/04A 2001-07-25 2002-07-18 Viral polymerase inhibitors RS50843B (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US30767401P 2001-07-25 2001-07-25
US33806101P 2001-12-07 2001-12-07
PCT/CA2002/001128 WO2003010141A2 (en) 2001-07-25 2002-07-18 Hepatitis c virus polymerase inhibitors with a heterobicyclic structure

Publications (2)

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RS7004A RS7004A (en) 2006-12-15
RS50843B true RS50843B (en) 2010-08-31

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YUP-69/04A RS51083B (en) 2001-07-25 2002-07-18 Viral polymerase inhibitors
YUP-70/04A RS50843B (en) 2001-07-25 2002-07-18 Viral polymerase inhibitors
RSP-2009/0517A RS20090517A (en) 2001-07-25 2002-07-18 Viral polymerase inhibitors

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KR (3) KR101031183B1 (en)
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AT (2) ATE382348T1 (en)
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CO (2) CO5650161A2 (en)
CY (2) CY1107354T1 (en)
DE (2) DE60224401T2 (en)
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PL (2) PL368357A1 (en)
PT (2) PT1414797E (en)
RS (3) RS51083B (en)
SG (1) SG176999A1 (en)
SI (2) SI1414441T1 (en)
UA (1) UA84256C2 (en)
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WO (2) WO2003010141A2 (en)

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